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hexyl mercaptan
Hexyl mercaptan is a sulfur-containing compound known for its burnt and roasted odor, used primarily as a flavoring agent in food products.
General Material Description
Hexyl mercaptan, also known as 1-hexanethiol among multiple synonyms, belongs to the thiol class of sulfur-containing organic compounds. It appears as a colorless liquid with a distinct burnt, sulfurous odor characterized by roasted and meaty nuances. This compound's molecular formula is C6H14S, reflecting the presence of six carbon atoms, fourteen hydrogens, and a sulfur atom. Sensory evaluations describe it as having intense roasted, nutty, and alliaceous characteristics at low parts-per-million concentrations. Hexyl mercaptan is naturally present in cooked meats like beef, chicken, and pork, contributing to their aroma profiles. It is commercially sourced and used mainly as a flavoring agent in various food products. For comprehensive chemical data, it is linked under controlled vocabularies such as ChEBI.
Occurrence, Applicability & Potential Uses
Hexyl mercaptan naturally occurs in cooked meats including beef, chicken, and pork, where it contributes to characteristic roasted and sulfurous aroma notes. Its presence is significant in the sensory profile of these foods due to its pronounced burnt and meaty nuances. The compound serves as a flavoring agent enhancing complex food flavors such as chocolate, coffee, fruits, and various meat products. Usage levels in food are guided by standards like FEMA (US), which classify hexyl mercaptan as generally recognized as safe (GRAS) for flavor use within defined limits. It is not approved for fragrance applications. These regulatory frameworks ensure controlled application in flavor formulations where hexyl mercaptan can provide desirable roasted, sulfurous, and savory characteristics.
Physico-Chemical Properties Summary
Hexyl mercaptan exhibits properties influential in its handling and application within flavor formulations. The compound has a boiling point ranging approximately from 150 to 154 °C at standard atmospheric pressure, enabling volatility suitable for flavor release. Its flash point is about 20.5 °C (69 °F), indicating moderate flammability requiring careful storage. The specific gravity at 20 °C lies between 0.842 and 0.846, a value affecting formulation density. Its refractive index ranges from 1.448 to 1.452 at 20 °C, relevant for purity assessment. The vapor pressure at 25 °C is 4.497 mmHg, reflecting moderate volatility. Hexyl mercaptan is soluble in alcohol and oils but shows limited solubility in water, with an estimated 177.1 mg/L at 25 °C. These physicochemical characteristics affect its incorporation and behavior in flavor systems, emphasizing proper formulation techniques to maintain stability and efficacy.
FAQ
What is hexyl mercaptan and what are its main characteristics?
Hexyl mercaptan, also known as 1-hexanethiol, is an organic sulfur compound characterized by a molecular formula of C6H14S. It is a colorless liquid with a pronounced burnt, sulfurous, and roasted odor. This compound is recognized for its contribution to the aroma profile of cooked meats such as beef, chicken, and pork. It has multiple synonyms including hexane-1-thiol and 1-mercaptohexane. Sensory descriptions highlight its intense roasted and savory notes at very low concentrations, making it significant in flavor chemistry.
How is hexyl mercaptan used and where is it typically found?
Hexyl mercaptan occurs naturally in cooked meats like beef, chicken, and pork, where it contributes roasted and sulfurous aroma qualities. It is primarily employed as a flavoring agent in food products to provide complex notes reminiscent of meat, roasted foods, chocolate, and various fruits. Its application is carefully controlled due to its intense odor and chemical properties. Regulatory bodies such as FEMA (US) provide guidelines on its safe use levels in flavor formulations, excluding its use in fragrances. The compound's moderate volatility and solubility in oils and alcohols facilitate its incorporation into diverse flavor systems.
What regulations and safety considerations apply to hexyl mercaptan?
Hexyl mercaptan is regulated under standards such as FEMA (US), which classify it as a flavoring substance generally recognized as safe (GRAS) within specified usage limits. It is not authorized for fragrance use due to its sensory properties. Safety data indicate it is flammable with a flash point around 20.5 °C and poses irritation risks to eyes, skin, and respiratory systems. Handling recommendations include avoidance of inhalation and skin contact, use of protective equipment, and storage away from ignition sources. Toxicological data report oral and inhalation toxicity values from animal studies, and safety guidelines are available from sources like the European Food Safety Authority and occupational health agencies.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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Other Information
| (IUPAC): | Atomic Weights of the Elements 2011 (pdf) |
| Videos: | The Periodic Table of Videos |
| tgsc: | Atomic Weights use for this web site |
| (IUPAC): | Periodic Table of the Elements |
| FDA Substances Added to Food (formerly EAFUS): | View |
| CHEBI: | View |
| CHEMBL: | View |
| HMDB (The Human Metabolome Database): | HMDB39806 |
| FooDB: | FDB019456 |
| Export Tariff Code: | 2930.90.9190 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
| Wikipedia: | View |
| FAO: | 1-Hexanethiol |
General Material Information
| Preferred name | hexyl mercaptan |
| Trivial Name | 1-Hexanethiol |
| Short Description | 1-hexanethiol |
| Formula | C6 H14 S |
| CAS Number | 111-31-9 |
| FEMA Number | 3842 |
| Flavis Number | 12.132 |
| ECHA Number | 203-857-0 |
| FDA UNII | 1KH2129A0Q |
| Nikkaji Number | J43.519H |
| Beilstein Number | 1731295 |
| MDL | MFCD00004909 |
| COE Number | 11487 |
| NMR Predictor | External link |
| JECFA Food Flavoring | 518 1-hexanethiol |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 111-31-9 ; 1-HEXANETHIOL |
| Synonyms |
|
Suppliers
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 118.24257659912 |
| Specific gravity | @ 20 °C |
| Pounds per Gallon | 7.014 to 7.048 |
| Refractive Index | 1.448 to 1.452 @ 20 °C |
| Melting Point | -81 to -80°C @ 760 mm Hg |
| Boiling Point | 150 to 154°C @ 760 mm Hg |
| Vapor Pressure | 4.497 mmHg @ 25 °C |
| Flash Point TCC Value | 20.56 °C TCC |
| logP (o/w) | 3.48 est |
| Solubility | |
| alcohol | Yes |
| oil | Yes |
| water, 177.1 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Burnt | |
| burnt, fatty, sulfurous, meaty, garlic, roasted, alliaceous, nutty | |
| General comment | At 0.10 % in propylene glycol. burnt fat sulfury meaty fatty garlic roasted burnt |
| Mosciano, Gerard P&F 25, No. 3, 25, (2000) | At 1.00 %. Intense roasted meaty, sulfurous and slightly alliaceous with roasted meaty and nutty nuance |
| Flavor Type: Roasted | |
| roasted, burnt, meaty, fatty, rubbery, sulfurous, vegetable | |
| Mosciano, Gerard P&F 25, No. 3, 25, (2000) | At 1.00 - 3.00 ppm. Roasted burnt meat with a fatty, rubbery and sulfurous vegetative nuance |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Odor purposes | Fruit , Passion fruit |
| Flavoring purposes | Chocolate , Coffee , Cucumber , Currant black currant , Fish , Mango , Meat , Peach , Peanut , Pepper bell pepper , Tomato |
Safety Information
Safety information
| Preferred SDS: View | |
| European information : | |
| Most important hazard(s): | |
| Xn - Harmful. | |
| R 10 - Flammable. R 20/22 - Harmful by inhalation and if swallowed. R 36/37/38 - Irritating to eyes, respiratory system, and skin. S 02 - Keep out of the reach of children. S 16 - Keep away from sources of ignition - No Smoking. S 20/21 - When using do not eat, drink or smoke. S 23 - Do not breath vapour. S 24/25 - Avoid contact with skin and eyes. S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S 36/37/39 - Wear suitable clothing, gloves and eye/face protection. | |
| Hazards identification | |
| Classification of the substance or mixture | |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) | |
| None found. | |
| GHS Label elements, including precautionary statements | |
| Pictogram | |
| Hazard statement(s) | |
| None found. | |
| Precautionary statement(s) | |
| None found. | |
| Oral/Parenteral Toxicity: | |
| intraperitoneal-mouse LD50 200 mg/kg National Technical Information Service. Vol. AD277-689 intraperitoneal-mouse LD50 1254 mg/kg LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION BEHAVIORAL: COMA BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) American Industrial Hygiene Association Journal. Vol. 19, Pg. 171, 1958. intraperitoneal-rat LD50 396 mg/kg LUNGS, THORAX, OR RESPIRATION: CYANOSIS BEHAVIORAL: MUSCLE WEAKNESS BEHAVIORAL: ATAXIA American Industrial Hygiene Association Journal. Vol. 19, Pg. 171, 1958. | |
| Dermal Toxicity: | |
| Not determined | |
| Inhalation Toxicity: | |
| inhalation-mouse LC50 528 ppm/4H SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) American Industrial Hygiene Association Journal. Vol. 19, Pg. 171, 1958. inhalation-rat LC50 1080 ppm/4H BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION American Industrial Hygiene Association Journal. Vol. 19, Pg. 171, 1958. | |
Safety in use information
| Category: | |||
| flavoring agents | |||
| Recommendation for hexyl mercaptan usage levels up to: | |||
| not for fragrance use. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | ND (μg/capita/day) | ||
| Structure Class: | I | ||
| Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS). | |||
| The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library | |||
| publication number: 18 | |||
| Click here to view publication 18 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | 0.10000 | 5.00000 | |
| beverages(nonalcoholic): | 0.10000 | 5.00000 | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | 0.10000 | 5.00000 | |
| cheese: | - | - | |
| chewing gum: | - | - | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | 0.10000 | 5.00000 | |
| fruit ices: | - | - | |
| gelatins / puddings: | - | - | |
| granulated sugar: | - | - | |
| gravies: | 0.10000 | 5.00000 | |
| hard candy: | - | - | |
| imitation dairy: | - | - | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | - | |
| meat products: | 0.10000 | 5.00000 | |
| milk products: | 0.10000 | 5.00000 | |
| nut products: | - | - | |
| other grains: | - | - | |
| poultry: | - | - | |
| processed fruits: | - | - | |
| processed vegetables: | - | - | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | 0.50000 | 5.00000 | |
| snack foods: | - | - | |
| soft candy: | 0.10000 | 5.00000 | |
| soups: | 0.10000 | 5.00000 | |
| sugar substitutes: | - | - | |
| sweet sauces: | 0.10000 | 5.00000 | |
Safety references
| European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies... |
| European Food Safety Authority (EFSA) reference(s): |
| Flavouring Group Evaluation 8 (FGE.08)[1]: Aliphatic and alicyclic mono-, di-, tri-, and polysulphides with or without additional oxygenated functional groups from chemical group 20 View page or View pdf |
| Flavouring Group Evaluation 8, Revision 1 (FGE.08Rev1): Aliphatic and alicyclic mono-, di-, tri-, and polysulphides with or without additional oxygenated functional groups from chemical groups 20 and 30 View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 8, Revision 3 (FGE.08Rev3): Aliphatic and alicyclic mono-, di-, tri-, and polysulphides with or without additional oxygenated functional groups from chemical groups 20 and 30 View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 08, Revision 4 (FGE.08Rev4): Aliphatic and alicyclic mono-, di-, tri-, and polysulphides with or without additional oxygenated functional groups from chemical groups 20 and 30 View page or View pdf |
| EPI System: View |
| NIOSH International Chemical Safety Cards:search |
| NIOSH Pocket Guide:search |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):111-31-9 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :8106 |
| National Institute of Allergy and Infectious Diseases:Data |
| WISER:UN 3336 |
| WGK Germany:3 |
| hexane-1-thiol |
| Chemidplus:0000111319 |
| EPA/NOAA CAMEO:hazardous materials |
| RTECS:111-31-9 |